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Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A.

Organic & biomolecular chemistry (2010-09-08)
José Antonio Morales-Serna, Ericka Sánchez, Ricardo Velázquez, Jorge Bernal, Eréndira García-Ríos, Rubén Gaviño, Guillermo Negrón-Silva, Jorge Cárdenas
ABSTRACT

A facile and mild macrolactonization reaction of ω-hydroxy acids was developed based on the transesterification of benzotriazole esters. Treatment of ω-hydroxy acids with 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) and 1-hydroxy benzotriazole (HOBT) in chloroform provided macrolactones in excellent yields. The reactions were performed under basic, neutral and acidic conditions using N,N-dimethylaminopyridine (DMAP), tetrabutylammonium tetrafluoroborate (TBABF(4)) and BF(3)·Et(2)O, respectively. A calcined hydrotalcite was also used instead of DMAP. Finally, to test the scope of the protocol in the synthesis of biologically relevant macrolactones, the total synthesis of Sansalvamide A was carried out.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
10-Hydroxydecanoic acid, technical grade
Sigma-Aldrich
Tetrabutylammonium tetrafluoroborate, 99%